Family Road Trip: Northern Lakes, Tuscany & Italian Riviera – 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You’ll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you’ll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.
Highlights
- Cruise past the luxury villas of Lake Como
- Ride a horse-drawn wagon through Tuscan hills
- Experience history in the medieval city of Siena
- Relax on a sunset boat tour of colorful Cinque Terre
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Milan, Transfer to Lake Como, and Como, Bellagio & Villas Boat Tour | Lake Como |
| Day 2 | Free Day in Lake Como Villages | Lake Como |
| Day 3 | Lake Como to Lake Garda, West Lake Garda & Sirmione Boat Tour | Lake Garda |
| Day 4 | Free Day on Lake Garda | Lake Garda |
| Day 5 | Lake Garda to Chianti, Chianti Wagon Ride & Picnic | Chianti |
| Day 6 | Explore Tuscany | Chianti |
| Day 7 | Chianti to San Gimignano & Monteriggioni | San Gimignano |
| Day 8 | Day Trip to Volterra | San Gimignano |
| Day 9 | San Gimignano to Siena & Explore Siena | Siena |
| Day 10 | Day Trip to Florence | Siena |
| Day 11 | Siena to Italian Riviera & Explore Genoa | Italian Riviera |
| Day 12 | Free Day on the Italian Riviera | Italian Riviera |
| Day 13 | Sunset Boat Trip & Cinque Terre Villages | Italian Riviera |
| Day 14 | Italian Riviera to Milan & Depart |
Detailed Itinerary
Day 1: Arrive in Milan, Transfer to Lake Como, and Como, Bellagio & Villas Boat Tour

Once you arrive, set out on a guided tour starting at Piazza Cavour, in Como’s historical center, before taking a semi-private cruise around the lake. You’ll see why Lake Como has been attracting nobility since Roman times when Julius Caesar founded Novum Comum (Como city). Your guide will lead you through tales of fortresses and castles, furious naval battles, and crowned monarchs who built villas with large Baroque or Romantic gardens. Take in the views of these villas, such as Villa Olmo, Villa D’Este, Villa Versace, Villa del Balbianello, and Villa Carlotta, as well as the towns of Cernobbio and Tremezzo.
Then, board your vessel for a look into the lake’s secret corners. No trip here is complete without some time on the water. Enjoy breathtaking views over the lake as well as its architectural wonders and villas, before you disembark in famous Bellagio, the area’s most-visited town.
In Bellagio, you’ll learn from your guide about key sights like Punta Spartiviento, the Romanesque Basilica of San Giacomo, and Via Roma. The town has been drawing visitors since the Renaissance when it was a center of industries—particularly silk—thanks to its ideal location. Stop at a hidden 18th-century cellar for local charcuterie tasting, then take a stroll through the boutiques to see how it still excels in silk products today.
Get lost in the colorful streets of the old town and enjoy the views over the lake. Then pay a visit to the gardens of Villa Melzi, where you’ll be greeted by Moorish architecture, water lilies, and even more lake views before your tour ends.
Day 2: Free Day in Lake Como Villages

Explore other villages to the north by ferry or car. The resort town of Bellagio is north of Como and sits on a promontory that juts into the lake. Lake Como splits three ways at this spot, offering spectacular scenic views. Varenna is another picturesque village to the east of Bellagio. A short ferry ride brings you to the town’s promenade along Lake Como, and the chance to visit Villa Monastero and the botanical gardens. If you have the time, consider visiting Lecco and Menaggio.
Day 3: Lake Como to Lake Garda, West Lake Garda & Sirmione Boat Tour

Once you reach Lake Garda, immerse yourself in the local history and nature with a relaxing private boat cruise. As you glide through the calm waters surrounded by beautiful scenery, you’ll view Salò, Garda Island, and Gardone, plus enjoy swimming from the boat.
Departing from the Sirmione Peninsula, you’ll head toward the impressive outcrop of Rocca di Manerba and pass the island of San Biagio. Next, cruise near the enchanting Isola del Garda, the private residence of the counts of Borghese-Cavazza. Lastly, make your way to the magnificent Costa Romantica, which boasts spectacular villas overlooking the lake and surrounded by lush vegetation.
Day 4: Free Day on Lake Garda

Day 5: Lake Garda to Chianti, Chianti Wagon Ride & Picnic

Along the way, you’ll pass several fascinating cities worth a stop. Enjoy Verona for its romantic setting in Romeo and Juliet, Mantua for its Renaissance history, and Modena and Bologna for their gastronomy, including the famed balsamic vinegar. You can also explore some of the area’s hilltop towns and vineyards.
You’ll meet your driver and guide and board your wagon. As you make your way through the Chianti countryside, enjoy breathing in the clean, fresh, and aromatic air in an open-air wagon. Two powerful horses lead you, crossing panoramic routes and historic castles. Your guide will entertain you with stories, interesting facts, and local myths.
Take a break at a shaded spot amongst Tuscany’s vineyards, enjoy a fresh picnic lunch of local products, and take in the panoramic views of this iconic landscape before heading back through more scenic Tuscan countryside.
Chat with a local specialist who can help organize your trip.
Day 6: Explore Tuscany

Visit family-friendly spots in the Chianti Valley like Val D’Elsa around San Gimignano, and Val D’Orcia around Pienza and Montepulciano. Throughout the incredibly scenic drive, you’ll be surrounded by olive groves and vineyards that make up the typical hilly landscape. The route is a combination of main roads and winding hilltop lanes as you make your way through the Tuscan countryside, and can take between a half and a full day to complete depending on how many stops you make.
Day 7: Chianti to San Gimignano & Monteriggioni

Enjoy a scenic drive from Chianti to San Gimignano, which takes about one hour. Along the way, enjoy your time exploring the beautiful landscape, hilltop towns, charming villages, and, of course, the vineyards. Stop to visit some of the region’s acclaimed castles and museums.
San Gimignano is famous for its tall, medieval towers. A UNESCO World Heritage Site since 1990, the charming hilltop town once housed 72 tower-houses, built as symbols of wealth and power of aristocratic families during the 13th and 14th centuries.
Be sure to make a stop to visit the impressive medieval fortress of Monteriggioni. The intact castle walls surround this town perched on a hillside and are a sight to behold. Take in the views, have a coffee, and enjoy wandering around the porticos and piazzas in the charming historic center.
Day 8: Day Trip to Volterra

Day 9: San Gimignano to Siena & Explore Siena

Day 10: Day Trip to Florence

Pop over to neighboring Florence for the day. You’ll find some of the world’s most recognizable art and architecture here, from Michelangelo’s “David” and Botticelli’s “Birth of Venus” to the 1,000-year-old Ponte Vecchio medieval bridge. If you’re looking for something more hands-on, visit the Leonardo da Vinci Museum, which is as interactive as the man himself would want, or consider the celestial spheres at the Museo Galileo, where you can peer through ancient telescopes.
The charms of Florence aren’t just found in its museums. Check out the many parks and gardens, including the Iris Garden that holds 250 endangered species, rambling markets, and celebrate the city’s status as the capital of gelato with as many scoops as you can handle.
Day 11: Siena to Italian Riviera & Explore Genoa

Via Garibaldi is the most famous street in Genoa, with many extravagant and luxurious Renaissance palaces open to the public. You can purchase a ticket to enter all the Rolli Palaces, which together make up the Strada Nuova Museums. Each one is unique and spectacular and together, they are a UNESCO World Heritage Site. Down by the port, you can spend time at the Maritime museum before heading into the historic city center.
Day 12: Free Day on the Italian Riviera

Day 13: Sunset Boat Trip & Cinque Terre Villages

Day 14: Italian Riviera to Milan & Depart

Map

Map of Family Road Trip: Northern Lakes, Tuscany & Italian Riviera – 14 Days
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